5. Advanced Penetration Testing for Highly-Secured Environments: The Ultimate Security Guide

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    Chapter 1: Planning and Scoping for a Successful Penetration Test
    Introduction to advanced penetration testing
    Vulnerability assessments
    Penetration testing
    Advanced penetration testing
    Before testing begins
    Determining scope
    Setting limits — nothing lasts forever
    Rules of engagement documentation
    Planning for action
    Installing VirtualBox
    Installing your BackTrack virtual machine
    Preparing the virtual guest machine for BackTrack
    Installing BackTrack on the virtual disk image
    Exploring BackTrack
    Logging in
    Changing the default password
    Updating the applications and operating system
    Installing OpenOffice
    Effectively manage your test results
    Introduction to MagicTree
    Starting MagicTree
    Adding nodes
    Data collection
    Report generation
    Introduction to the Dradis Framework
    Exporting a project template
    Importing a project template
    Preparing sample data for import
    Importing your Nmap data
    Exporting data into HTML
    Dradis Category field
    Changing the default HTML template
    Summary

    Chapter 2: Advanced Reconnaissance Techniques
    Introduction to reconnaissance
    Reconnaissance workflow
    DNS recon
    Nslookup — it's there when you need it
    Default output
    Changing nameservers
    Creating an automation script
    What did we learn?
    Domain Information Groper (Dig)
    Default output
    Zone transfers using Dig
    Advanced features of Dig
    DNS brute forcing with fierce
    Default command usage
    Creating a custom wordlist
    Gathering and validating domain and IP information
    Gathering information with whois
    Specifying which registrar to use
    Where in the world is this IP?
    Defensive measures
    Using search engines to do your job for you
    SHODAN
    Filters
    Understanding banners
    Finding specific assets
    Finding people (and their documents) on the web
    Google hacking database
    Metagoofil
    Searching the Internet for clues
    Metadata collection
    Extracting metadata from photos using exiftool
    Summary

    Chapter 3: Enumeration: Choosing Your Targets Wisely
    Adding another virtual machine to our lab
    Configuring and testing our Vlab_1 clients
    BackTrack – Manual ifconfig
    Ubuntu – Manual ifconfig
    Verifying connectivity
    Maintaining IP settings after reboot
    Nmap — getting to know you
    Commonly seen Nmap scan types and options
    Basic scans — warming up
    Other Nmap techniques
    Remaining stealthy
    Shifting blame — the zombies did it!
    IDS rules, how to avoid them
    Using decoys
    Adding custom Nmap scripts to your arsenal
    How to decide if a script is right for you
    Adding a new script to the database
    SNMP: A goldmine of information just waiting to be discovered
    SNMPEnum
    SNMPCheck
    When the SNMP community string is NOT "public"
    Creating network baselines with scanPBNJ
    Setting up MySQL for PBNJ
    Starting MySQL
    Preparing the PBNJ database
    First scan
    Reviewing the data
    Enumeration avoidance techniques
    Naming conventions
    Port knocking
    Intrusion detection and avoidance systems
    Trigger points
    SNMP lockdown
    Summary

    Chapter 4: Remote Exploitation
    Exploitation – Why bother?
    Target practice – Adding a Kioptrix virtual machine
    Manual exploitation
    Enumerating services
    Quick scan with Unicornscan
    Full scan with Nmap
    Banner grabbing with Netcat and Ncat
    Banner grabbing with Netcat
    Banner grabbing with Ncat
    Banner grabbing with smbclient
    Searching Exploit-DB
    Exploit-DB at hand
    Compiling the code
    Compiling the proof of concept code
    Troubleshooting the code
    Running the exploit
    Getting files to and from victim machines
    Installing and starting a TFTP server on BackTrack 5
    Installing and configuring pure-ftpd
    Starting pure-ftpd
    Passwords: Something you know
    Cracking the hash
    Brute forcing passwords
    THC Hydra
    Metasploit — learn it and love it
    Updating the Metasploit framework
    Databases and Metasploit
    Installing PostgreSQL on BackTrack 5
    Verifying database connectivity
    Performing an Nmap scan from within Metasploit
    Using auxiliary modules
    Using Metasploit to exploit Kioptrix
    Summary

    Chapter 5: Web Application Exploitation
    Practice makes perfect
    Installing Kioptrix Level 3
    Creating a Kioptrix VM Level 3 clone
    Installing and configuring Mutillidae 2.1.7 on the Ubuntu virtual machine
    Installing and configuring pfSense
    Preparing the virtual machine for pfSense
    pfSense virtual machine persistence
    Configuring the pfSense DHCP server
    Starting the virtual lab
    pfSense DHCP – Permanent reservations
    Installing HAProxy for load balancing
    Adding Kioptrix3.com to the host file
    Detecting load balancers
    Quick reality check – Load Balance Detector
    So, what are we looking for anyhow?
    Detecting Web Application Firewalls (WAF)
    Taking on Level 3 – Kioptrix
    Web Application Attack and Audit Framework (w3af)
    Using w3af GUI to save time
    Scanning by using the w3af console
    Using WebScarab as a HTTP proxy
    Introduction to Mantra
    Summary

    Chapter 6: Exploits and Client-Side Attacks
    Buffer overflows—A refresher
    "C"ing is believing—Create a vulnerable program
    Turning ASLR on and off in BackTrack
    Understanding the basics of buffer overflows
    Introduction to fuzzing
    Introducing vulnserver
    Fuzzing tools included in BackTrack
    Bruteforce Exploit Detector (BED)
    SFUZZ: Simple fuzzer
    Fast-Track
    Updating Fast-Track
    Client-side attacks with Fast-Track
    Social Engineering Toolkit
    Summary

    Chapter 7: Post-Exploitation
    Rules of engagement
    What is permitted?
    Can you modify anything and everything?
    Are you allowed to add persistence?
    How is the data that is collected and stored
    handled by you and your team?
    Employee data and personal information
    Data gathering, network analysis, and pillaging
    Linux
    Important directories and files
    Important commands
    Putting this information to use
    Enumeration
    Exploitation
    Were connected, now what?
    Which tools are available on the remote system
    Finding network information
    Determine connections
    Checking installed packages
    Package repositories
    Programs and services that run at startup
    Searching for information
    History files and logs
    Configurations, settings, and other files
    Users and credentials
    Moving the files
    Microsoft Windows™ post-exploitation
    Important directories and files
    Using Armitage for post-exploitation
    Enumeration
    Exploitation
    Were connected, now what?
    Networking details
    Finding installed software and tools
    Pivoting
    Summary

    Chapter 8: Bypassing Firewalls and Avoiding Detection
    Lab preparation
    BackTrack guest machine
    Ubuntu guest machine
    pfSense guest machine configuration
    pfSense network setup
    WAN IP configuration
    LAN IP configuration
    Firewall configuration
    Stealth scanning through the firewall
    Finding the ports
    Traceroute to find out if there is a firewall
    Finding out if the firewall is blocking certain ports
    Now you see me, now you don't — Avoiding IDS
    Canonicalization
    Timing is everything
    Blending in
    Looking at traffic patterns
    Cleaning up compromised hosts
    Using a checklist
    When to clean up
    Local log files
    Miscellaneous evasion techniques
    Divide and conquer
    Hiding out (on controlled units)
    File integrity monitoring
    Using common network management tools to do the deed
    Summary

    Chapter 9: Data Collection Tools and Reporting
    Record now — Sort later
    Old school — The text editor method
    Nano
    VIM — The power user's text editor of choice
    NoteCase
    Dradis framework for collaboration
    Binding to an available interface other than 127.0.0.1
    The report
    Challenge to the reader
    Summary

    Chapter 10: Setting Up Virtual Test Lab Environments
    Why bother with setting up labs?
    Keeping it simple
    No-nonsense test example
    Network segmentation and firewalls
    Requirements
    Setup
    Adding complexity or emulating target environments
    Configuring firewall1
    Installing additional packages in pfSense
    Firewall2 setup and configuration
    Web1
    DB1
    App1
    Admin1
    Summary

    Chapter 11: Take the Challenge – Putting It All Together
    The scenario
    The setup
    NewAlts Research Labs' virtual network
    Additional system modifications
    Web server modifications
    The challenge
    The walkthrough
    Defining the scope
    Determining the "why"
    So what is the "why" of this particular test?
    Developing the Rules of Engagement document
    Initial plan of attack
    Enumeration and exploitation
    Reporting
    Summary
    Index

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